Periampullary tumors are cancers that arise in the region of the ampulla of Vater, where the bile duct and pancreatic duct converge and empty into the small intestine. These tumours can be challenging to diagnose and manage given the region's transitional character and closeness to various structures. Upper gastrointestinal bleeding may be a rare clinical presentation following tumoral ulceration, erosion into blood vessels or nearby structures or secondary complications like pancreatitis or portal hypertension. Identifying the anatomical origin of these malignancies is usually a herculean task. This will require prompt oesophagogastroduodenoscopy and imaging to determine the source. Immunohistochemistry may be helpful in differentiating these tumours. We present periampullary tumour an unusual cause of upper gastrointestinal bleeding. A 52 year old male was admitted for evaluation following a 3 months history of weight loss, burning/colicky epigastric pain, easy fatiguability, dizziness, vomiting and passage of malaena.He was fully conscious on admission, pale, tachycardic with a blood pressure of 90/70mmHg. He had an international normalized ratio (INR) of 1.0. Oesophagogastroduodenoscopy showed a polypoid fungating mass at the1st and 2nd parts of the duodenum. A Computerized Tomogram scan of the abdomen showed a diffuse circumferential duodenal wall thickening of 1st and 2nd parts with reduction in luminal calibre, mildly dilated pancreatic, common bile and common hepatic ducts. Histology showed moderately differentiated adenocarcinoma. He had a side to side gastrojejunal anastomosis and cholecystojejunostomy and entero-enterotomy following which he received chemotherapy.